Dichloromethane → 5,5-dimethyl-6-oxo-6-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-hexanenitrile

HRID 1677522노트

반응식

HRID 1677522 반응식
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:20])[C:12]([CH3:19])([CH3:18])[CH2:13][CH2:14][CH2:15][C:16]#[N:17])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:21][O:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:18][C:12]([CH3:19])([C:11](=[O:20])[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:25]3[CH:26]=[C:27]([O:31][CH3:32])[C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[CH:24]=3)[N:3]=2)[NH:8][CH:9]=1)[CH2:13][CH2:14][CH2:15][C:16]#[N:17]

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 595407676-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,5-dimethyl-6-oxo-hexanenitrile

생성물 1

HCID 595407395,5-dimethyl-6-oxo-6-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-hexanenitrile수율 4%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 6-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,5-dimethyl-6-oxo-hexanenitrile (0.079 g, 0.236 mmol), 3,4,5-trimethoxyphenylboronic acid (0.055 g, 0.26 mmol), potassium carbonate (0.098 g, 0.71 mmol) and Pd(dppf)Cl2.CH2Cl2 (0.019 g, 0.024 mmol) in 2.4 mL of 1,4-dioxane and 0.4 mL of water was stirred at 120° C. in a microwave for 1 h, then at 130° C. in a microwave for 1 h. The resulting mixture was partitioned between 50 mL of ethyl acetate and 25 mL of water. The organic layer was dried over MgSO4, filtered, and concentrated to a residue. Column chromatography (0→100% EtOAc/hexanes) afforded 0.004 g (4%) of 5,5-dimethyl-6-oxo-6-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-hexanenitrile as a white solid.

후처리

  1. customThe resulting mixture was partitioned between 50 mL of ethyl acetate and 25 mL of water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a residue

출처 및 근거

ORD 기록
ord-096b93453aab47e6a0cf25c7f77b20a2
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008298B2

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